Triphenylphosphine → 5-Chloro-2-methoxybenzene-1-thiol

HRID 1675590Notes

Reaction equation

HRID 1675590 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:31][CH3:32])=[C:25]([S:27](Cl)(=O)=O)[CH:26]=1>C1COCC1.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:31][CH3:32])=[C:25]([SH:27])[CH:26]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 127727855-Chloro-2-methoxybenzene-1-thiol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (11.4 g) was added portionwise to a stirred solution of 5-chloro-2-methoxybenzenesulphonyl chloride (3.0 g) in THF (30 ml). Water (4 ml) was added and the mixture stirred at RT for 2 h, after which the reaction was diluted with water (25 ml) then 2M sodium hydroxide solution and washed with ether. The aqueous layer was acidified with 2M hydrochloric acid and extracted with ethylacetate. The organic layer was dried and evaporated under reduced pressure, yield 3.1 g.

Workup

  1. wash2M sodium hydroxide solution and washed with ether
  2. extractionextracted with ethylacetate
  3. customThe organic layer was dried
  4. customevaporated under reduced pressure, yield 3.1 g

Sources & evidence

ORD record
ord-c802e92cd8f549e28bc7519933a6f9ba
Source dataset
uspto-grants-2011_08
Patent number
US08003703B2

Reaction notes

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